Old Florida Trail

4.7 (6 reviews)

From $39

Go back in time and visit old Florida. You'll visit delightful small towns, dig into local fare, explore a few outdoor adventures, and fill up your camera roll with quirky photo ops.

When to Go Mon - Sat
ends near Gainesville, FL

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  • Free Shipping on Orders $100+
  • 30-Day Returns & Exchanges
  • No Booking Required

essentials for your trip

Mint Road Trip Journal

Mint Road Trip Journal

Track all your local adventures - big or small - in one place. With space...

Road Trip Tote Bag

Road Trip Tote Bag

An essential tote bag for your road trip ahead. Carry everything from your surprise package...

Trip Highlights

  • Visit 'blink-and-you'll-miss-it' charming, small towns
  • Delightful local sweets & eats
  • A number of short picturesque trails
  • A botanical garden that dreams are made of
  • Fruit-forward wines at a picturesque winery
  • Multiple recommendations included on every stop

How Long Is This Trip?

Please see the approximate driving distances below. Please note this just includes round-trip driving distances and not time spent at stops.

From Orlando:
3 hours and 40 minutes / 229 miles

From Tampa:
4 hours and 10 minutes / 264 miles

From Jacksonville:
3 hours and 39 minutes / 187 miles

From Tallahassee:
3 hours and 20 minutes / 337 miles

*We recommend booking an overnight hotel if the driving distance is greater than 4 hours round-trip.

When Can I Go?

Days of the week: Monday - Saturday preferred

Seasons: Year-round

Not recommended: Holidays, Sundays (see note)

Travel Tips

If you travel on a Sunday, note that a few spots will be closed or will open later.

Shipping & Returns

Shipping: Free shipping on orders over $100. Standard shipping takes 4–10 business days. Need it faster? Choose the fastest option at checkout for 2–4 business day delivery.

Returns: Not the right fit? Reach out within 30 days of purchase to start a return. Products just need to be unopened, unused, and in their original packaging, return shipping is your responsibility. Digital trips, gift cards, and opened products can't be returned.

Exchanges: Want a different trip instead? Email us at questions@guesswheretrips.com within 30 days of your order, there's a small $8 reshipping fee to send your new pick out. Digital trips cannot be exchanged.

Read our full return policy →

Old Florida Trail

4.7 Physical Package

Here's How It Works

Browse by location and find a surprise trip that fits your day. Every route is road-tested by our team.

Your surprise destinations stay sealed until you're ready for them. One envelope at a time on the road, all day long.

Hidden gems, local favorites, and stories you won't find on Google. That's what's waiting for you.

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Frequently Asked Questions

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Road Tested by Our Team

Our team spends 40+ hours researching, driving, and vetting every route: talking to locals, discovering hidden gems, and making sure every stop is worth your day.

We Remember Experiences, Not Things.

Research consistently shows that spending time together creates more lasting happiness than buying more stuff. Every Guess Where Trip is thoughtfully planned to help you reconnect, explore, and create memories that last long after the day is over.